Narcissine : an alkaloid from the bulb of the common daffodil (Narcissus pseudonarcissus) / by Arthur James Ewins.

  • Ewins, Arthur James.
Date:
1910
Catalogue details

Licence: Attribution 4.0 International (CC BY 4.0)

Credit: Narcissine : an alkaloid from the bulb of the common daffodil (Narcissus pseudonarcissus) / by Arthur James Ewins. Source: Wellcome Collection.

Provider: This material has been provided by The Royal College of Surgeons of England. The original may be consulted at The Royal College of Surgeons of England.

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    In view of these statements and of the fact that no reference to “ narcissia ” or to any alkaloid obtained from the bulbs of the daffodil can be found in chemical literature, it appeared to be of interest to obtain the alkaloid in a pure state, in order that a more detailed investigation of its chemical and physiological properties might be made, more especially as the alkaloids which have been obtained from monocotyledons are comparatively few in number. The bulbs of a cultivated variety of the daffodil (Narcissus princeps), being more readily obtainable than the variety mentioned above, were first employed in the investigation. From these bulbs, however, the extracts obtained from the resting or flowering bulbs gave only traces of alkaloidal reactions, and the isolation of the alkaloid was obviously hopeless. With the bulbs of the wild daffodil (Narcissus pseudonarcissus), much more satisfactory results were obtained. From these a crystalline alkaloid was readily obtained. From the resting bulbs a yield of approximately 0‘2 per cent, of the dried material, and from the flowering bulbs only about 0T per cent., was obtained. The alkaloid, which, in accordance with modern usage, it is suggested be called “ narcis«ine,” rather than “ narcissia,” was the same in both cases. Narcissine has been found by analyses and molecular-weight determination to possess the formula C10HI7O.,N. The alkaloid is characterised by very great stability, and on that account and owing to the small amount of material available (about 3 grams only), no light has been thrown on its probable constitution. The nitrogen present is tertiary, since nitrous acid is without action on the alkaloid, and treatment with methyl iodide produced an amorphous product which was probably the metliiodide of the base, but which could not be crystallised for analysis. The action of hydriodic acid (Zeisel) showed the absence of methoxy-groups, but on very strongly heating, a very small amount of methyl iodide was evolved, and the residue on suitable treatment yielded a solution which gave a violet coloration with ferric chloride, the phenolic substance being extracted from its acid solution by ether. The amount of substance so obtained was, however, extremely small, and further attempts to hydrolyse by means of acids yielded no crystalline product. Fusion with potassium hydroxide yielded no better results. At temperatures up to 220° the alkaloid was only very slowly attacked, traces of alkaline vapour being evolved. Heating with the naked flame for one and a-quarter hours was required in order to decompose completely about 0'7 gram of the alkaloid. The reaction product dissolved in water gave on addition of ferric chloride a violet cojoration, quickly passing to a dirty brown, with separation of a